Organic electronic element using a compound for organic electronic element, and an electronic device thereof

ABSTRACT

Provided are a compound of Formula 1 and an organic electric element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode and comprising the compound, the element showing improved luminescent efficiency, stability, and life span.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims benefit under 35 U.S.C. 119, 120, 121, or365, and is a National Stage entry from International Application No.PCT/KR2015/007474, filed Jul. 17, 2015, which claims priority to KoreanPatent Application No. 10-2014-0091658 filed on Jul. 21, 2014, thecontents of which are hereby incorporated by reference for all purposesas if fully set forth herein.

BACKGROUND

Technical Field

The present invention relates to organic electrical element usingcompound for organic electrical element, and electronic device thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer may have a multilayered structureincluding multiple layers made of different materials in order toimprove the efficiency and stability of an organic electric element, andfor example, may include a hole injection layer, a hole transport layer,a light emitting layer, an electron transport layer, an electroninjection layer, or the like.

A material used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

Currently, the power consumption is required more and more as size ofdisplay becomes larger and larger in the portable display market.Therefore, the power consumption is a very important factor in theportable display with a limited power source of the battery, andefficiency and life span issue also must be solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase. However, efficiency cannot be maximized only bysimply improving the organic material layer. This is because long lifespan and high efficiency can be simultaneously achieved when an optimalcombination of energy levels and T1 values, inherent material properties(mobility, interfacial properties, etc.), and the like among therespective layers included in the organic material layer is given.

Further, in order to solve the emission problem with a hole transportlayer in a recent organic electric element, an emission-auxiliary layeris formed between the hole transport layer and a light emitting layer,and it is time to develop different material of emission-auxiliarylayers according to respective pixel-domain(R, G, B) of light emittinglayers.

In general, an exciton is formed by recombination of an electron whichtransfers from an electron transport layer to a light emitting layer anda hole which transfers from a hole transport layer to the light emittinglayer.

However, it mainly has a low T1 value because a material used in a holetransporting layer should have a low HOMO value, thereby excitonsgenerated from a light emitting layer are transported to the holetransporting layer, resulting in a charge unbalance in the lightemitting layer. Thus, light emission occurs in the hole transportinglayer or at an interface of the hole transporting layer so that colorpurity, efficiency and lifespan of the organic electroluminescent deviceare reduced.

Further, when a material with rapid hole mobility is used in order toreduce a driving voltage in the organic electroluminescent device, itshows tendency to lower the efficiency. The general organic electricelement has a hole mobility higher than an electron mobility. Thiscauses a charge unbalance in the light emitting layer resulting in lowemitting efficiency and lifespan.

Therefore, in order to solve a problem of a hole transport layer, itneeds to form the light emitting layer as material which has a holetransport ability to have a proper driving voltage, high T1 (electronblock) value and wide bandgap.

These requirements are not satisfied only by structural characteristicsof a core of the emission-auxiliary layer material, and it is possibleto satisfy these requirements when characteristics of core and subsubstituents have an appropriate combination. Therefore, it is necessarystrongly to develop of the material for the emission-auxiliary layerhaving high T1 energy value and wide band gap, to improve efficiency andlifespan of the organic electric element.

In order to allow an organic electric element to fully exhibit theabove-mentioned excellent features, it should be prerequisite to supporta material forming an organic material layer of the element, forexample, a hole injection material, a hole transport material, a lightemitting material, an electron transport material, an electron injectionmaterial, an emission-auxiliary layer material or the like, by a stableand efficient material. However, such a stable and efficient organicmaterial layer material for an organic electric element has not yet beenfully developed. Accordingly, there is a continuous need to develop newmaterials for an organic material layer, specially, there are strongneeds to develop materials for an emission-auxiliary layer and a holetransport layer.

SUMMARY

In order to solve one or more of the above-mentioned problems occurringin the prior art, an aspect of the present invention provides an organicelectrical element comprising compound which can improve a luminescenceefficiency, lower a driving voltage, make thermal-resistance high, andimprove color purity and lifespan of the organic electrical element, andan electronic device including the organic electric element.

In accordance with an aspect of the present invention, there is providedan organic electrical element comprising the compound represented by thefollowing Formula, and an electronic device including the organicelectrical element.

In another aspect of the present invention, there is provided an organicelectrical element comprising a first electrode, a second electrode, andan organic material layer formed between the first electrode and thesecond electrode and comprising an emission-auxiliary layer and a lightemitting layer, wherein the emission-auxiliary layer comprises compoundrepresented by the above Formula.

By employing the compound of the present invention, the organicelectrical element according to one or more embodiments of the presentinvention can have improved luminescence efficiency, low drivingvoltage, high heat-resistant, improved color purity and lifespan.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component. In addition, itwill be understood that when an element such as a layer, film, region orsubstrate is referred to as being “on” or “over” another element, it canbe directly on the other element or intervening elements may also bepresent. In contrast, when an element is referred to as being “directlyon” another element, there are no intervening elements present.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine(F), chlorine(Cl), bromine(Br), iodine(I) and so on.

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means aliphaticfunctional radicals including a linear alkyl group, a branched chainalkyl group, a cyclo alkyl group (alicyclic), or an alkyl groupsubstituted with a cyclo alkyl.

Unless otherwise stated, the term “halo alkyl” or “halogen alkyl” asused herein includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cyclo alkyl” as used herein means,but not limited to, alkyl forming a ring having 3 to 60 carbon atoms.

The term “alkoxy group” or “alkyloxy group” as used herein means anoxygen radical attached to an alkyl group, but not limited to, and has 1to 60 carbon atoms.

The term “aryloxyl group” or “aryloxy group” as used herein means anoxygen radical attached to an aryl group, but not limited to, and has 6to 60 carbon atoms.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein means, univalent or bivalent functional groupwhich R, R′ and R″ are all hydrogen in the structural formula below.Also, “substituted fluorenyl group” or “substituted fluorenylene group”means, functional group which at least any one of R, R′ and R″ is afunctional group other than hydrogen and spiro compound which R and R′can be linked together with the carbon to which they are attached toform spiro compound.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. The arylgroup or arylene group include a monocyclic rings, ring assemblies,fused polycyclic system or spiro compounds.

Unless otherwise stated, the term “heterocyclic group” as used hereinmeans, but not limited to, a non-aromatic ring as well as an aromaticring like “heteroaryl group” or “heteroarylene group”. The heterocyclicgroup as used herein means, but not limited to, a ring containing one ormore heteroatoms, and having 2 to 60 carbon atoms. Unless otherwisestated, the term “heteroatom” as used herein represents at least one ofN, O, S, P and Si. The heterocyclic group means a monocyclic, ringassemblies, fused polycyclic system or spiro compound containing one ormore heteroatoms.

Also, the term “heterocyclic group” may include SO₂ instead of carbonconsisting of cycle. For example, “heterocyclic group” includes compoundbelow.

Unless otherwise stated, the term “ring” as used herein means, amonocyclic and polycyclic, an aliphatic ring and heterocyclic groupcontaining at least one heteroatom, and an aromatic ring and anon-aromatic ring.

Unless otherwise stated, the term “polycyclic” as used herein means,ring assemblies like biphenyl and terphenyl, fused polycyclic system andspiro compound, an aromatic ring and a non-aromatic ring, and analiphatic ring and heterocyclic group containing at least oneheteroatom.

Unless otherwise stated, the term “ring assemblies” as used hereinmeans, two or more cyclic systems (single rings or fused systems) whichare directly joined to each other by double or single bonds are namedring assemblies when the number of such direct ring junctions is oneless than the number of cyclic systems involved. The ring assembliesalso mean, same or different ring systems are directly joined to eachother by double or single bonds.

Unless otherwise stated, the term “fused polycyclic system” as usedherein means, fused ring type which has at least two atoms as the commonmembers, fused two or more aliphatic ring systems and a fused heteroring system containing at least one heteroatom. Fused polycyclic systemis an aromatic ring, a hetero aromatic ring, an aliphatic ring, or thecombination of these.

Unless otherwise stated, the term “spiro compound” as used herein has, aspiro union which means union having one atom as the only common memberof two rings. The common atom is designated as ‘spiro atom’. Thecompounds are defined as ‘monospiro-’, ‘dispiro-’ or ‘trispiro-’depending on the number of spiro atoms in one compound.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an aryl alkoxymeans an alkoxy substituted with an aryl, an alkoxyl carbonyl means acarbonyl substituted with an alkoxyl, and an aryl carbonyl alkenyl alsomeans an alkenyl substitutes with an aryl carbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthiophene group, a C₆-C₂₀ arylthiophene group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₆₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Otherwise specified, the Formulas used in the present invention are asdefined in the index definition of the substituent of the followingFormula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole R¹ is linked to any one of thecarbon atoms constituting the benzene ring, when a is an integer of 2 or3, the substituent R¹s may be the same and different each other, and arelinked to the benzene ring as follows. when a is an integer of 4 to 6,the substituents R¹s are linked to carbon atom of the benzene ring in asimilar manner to that. Meanwhile, hydrogen atoms linked to carbonconstituting the benzene ring may not be represented as usual.

FIG. 1 illustrates an organic electric element according to anembodiment of the present invention.

Referring to FIG. 1, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer therebetween which contains the inventive compound. Here,the first electrode 120 may be an anode (positive electrode), and thesecond electrode 180 may be a cathode (negative electrode). In the caseof an inverted organic electric element, the first electrode may be acathode, and the second electrode may be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, at least one of the layers may not be formed.The organic material layer may further include a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, a buffer layer141 and so on, and the electron transport layer 160 and the like mayserve as the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include at least oneprotective layer or one capping layer formed on at least one of thesides the first and second electrodes, which is a side opposite to theorganic material layer.

The inventive compound employed in the organic material layer may beused as materials of the hole injection layer 130, the hole transportlayer 140, the electron transport layer 160, the electron injectionlayer 170, the light emitting layer 150, a capping layer, anemission-auxiliary layer and so on. For example, the inventive compoundmay be used as materials of a hole transport layer 140 and/or anemission-auxiliary layer(151).

Meanwhile, since depending on the type of a substituent and position towhich a substituent is attached, a band gap, electrical properties,interfacial properties, and the like may vary even in the same core, itis very important what the types of core and a combination of core andsubstituent attached to the core. Specially, long life span and highefficiency can be simultaneously achieved when an optimal combination ofenergy levels and T1 values, inherent material properties (mobility,interfacial properties, etc.), and the like among the respective layersof the organic material layer is given.

As already described above, in order to solve the emission problem witha hole transport layer in a conventional organic electric element, anemission-auxiliary layer is preferably formed between the hole transportlayer and a light emitting layer, and it is necessary to form differentemission-auxiliary layers corresponding to respective light emittinglayers (R, G, B). Meanwhile, even when a similar core is used, it isvery difficult to infer the characteristics of an emission-auxiliarylayer if a used organic material layer varies because the correlationbetween the emission-auxiliary layer and a hole transport layer andbetween the emission-auxiliary layer and a light emitting layer (host)must be figured out.

Accordingly, in the present invention, energy levels, T1 values andinherent material properties (mobility, interfacial properties, etc.)among the respective organic material layers are optimized by forming ahole transport layer or/and an emission-auxiliary layer employing theinventive compounds, and thus the life span and efficiency of theorganic electric element can be improved at the same time.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate 110 toform the anode 120, forming the organic material layer including thehole injection layer 130, the hole transport layer 140, the lightemitting layer 150, the electron transport layer 160, and the electroninjection layer 170 thereon, and then depositing a material, which canbe used as the cathode 180, thereon. Also, an emission-auxiliary layer151 may be further formed between a hole transport layer 140 and a lightemitting layer 150.

Further, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, nozzle printing, inkjet printing, slot coating, dip coating,roll-to-roll, doctor blading, screen printing, or thermal transferprocess. Since the organic material layer according to the presentinvention may be formed in various ways, the scope of protection of thepresent invention is not limited by a method of forming the organicmaterial layer.

According to used materials, the organic electric element according toan embodiment of the present invention may be of a top emission type, abottom emission type, or a dual emission type.

A WOLED (White Organic Light Emitting Device) readily allows for theformation of ultra-high definition images, and is of excellentprocessability as well as enjoying the advantage of being produced usingconventional color filter technologies for LCDs. In this regard, variousstructures for WOLEDs, used as back light units, have been, in the mostpart, suggested and patented. Representative among the structures are aparallel side-by-side arrangement of R (Red), G (Green), B (Blue)light-emitting units, a vertical stack arrangement of RGB light-emittingunits, and a CCM (color conversion material) structure in whichelectroluminescence from a blue (B) organic light emitting layer, andphotoluminescence from an inorganic luminescent using theelectroluminescence are combined. The present invention is applicable tothese WOLEDs.

Further, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC), anorganic transistor (organic TFT), and an element for monochromatic orwhite illumination.

Another embodiment of the present invention provides an electronicdevice including a display device, which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, an organic electric element according to an aspect of thepresent invention will be described.

In accordance with an aspect of the present invention, there is providedan organic electric element comprising a first electrode, a secondelectrode, and an organic material layer which is formed between thefirst electrode and the second electrode and comprises at least anemission-auxiliary layer and a light emitting layer, wherein theemission-auxiliary layer comprises compound represented by the followingFormula 1.

In Formula 1, each symbol may be defined as follows.

In the Formula 1, Ar¹ to Ar⁵ may be each independently selected from thegroup consisting of a C₆-C₂₄ aryl group; a fluorenyl group; a C₂-C₂₅heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a fused ring formed by a C₃-C₂₄aliphatic ring and a C₆-C₂₄ aromatic ring; a C₁-C₂₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group and the combination thereof.

Preferably, Ar¹ to Ar⁴ may be each independently a C₆-C₁₂ aryl group, afluorenyl group, or a C₃-C₁₂ heterocyclic group, more preferably, aC₆-C₁₀ aryl group or a C₁₂ heterocyclic group, for example, phenyl,naphthyl, dibenzothiophene, dibenzofuran or a fluorenyl group and so on,and each of these may be further substituted with methyl or t-butyl.

Preferably, Ar⁵ may be a C₆-C₁₈ aryl group or a C₃-C₁₂ heterocyclicgroup, more preferably, a C₆-C₁₂ aryl group or a C₅-C₁₂ heterocyclicgroup, more preferably, a C₆, C₁₀, C₁₂ or C₁₈ aryl group or, a C₁₂heterocyclic group, for example, phenyl, naphthyl, biphenyl, terphenyl,dibenzothiophene and so on, and each of these may be further substitutedwith naphthyl or dibenzothiophene.

Preferably, Ar¹ to Ar⁵ may be substituted with one or more substituentsselected from the group consisting of deuterium; halogen; a silanegroup; a siloxane group; a boron group; a germanium group; a cyanogroup; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group; aC₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted with deuterium; afluorenyl group; a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si and P; aC₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.

L¹ and L² may be independently selected from the group consisting of asingle bond, a C₆-C₂₄ arylene group, a fluorenylene group, a C₂-C₂₄heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, a fused ring formed by a C₃-C₂₄aliphatic ring and a C₆-C₂₄ aromatic ring and the combination thereof.

Preferably, L¹ and L² may be independently a C₆-C₁₂ arylene group or aC₃-C₁₂ heterocyclic group and so on, more preferably, a C₆ arylenegroup, or a C₅ or C₁₂ heterocyclic group, and for example, a singlebond, phenyl, pyridine, dibenzothiophene and so on.

When L¹ and L² are each independently an arylene group, a fluorenylenegroup, a heterocyclic group or a fused ring, each of L¹ and L² may befurther substituted with one or more substituents selected from thegroup consisting of deuterium; halogen; a silane group; a siloxanegroup; a boron group; a germanium group; a cyano group; a nitro group; aC₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; aC₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si and P; a C₃-C₂₀ cycloalkylgroup; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀ arylalkenyl group.

Specifically, the compound of the emission-auxiliary layer representedby Formula 1 may be represented by any one of the following Formulas 2to 6.

In formulas 2 to 6, Ar¹ to Ar⁵, L¹ and L² may be each the same asdefined in Formula 1 above.

More specifically, the compound represented by Formula 1 may be any oneof the following compounds.

In another aspect of the present invention, there is provided an organicelectric element comprising a first electrode,

a second electrode, and an organic material layer formed between thefirst electrode and the second electrode, wherein the organic materiallayer comprises a hole transport layer, an emission-auxiliary layer anda light emitting layer and the emission-auxiliary comprises compoundrepresented by Formula Formula 7 below.

In Formula 7, each symbol may be defined as follows.

In the Formula 7, Ar⁶ and Ar⁷ may be independently selected from thegroup consisting of a C₆-C₆₀ aryl group; a fluorenyl group; aC₂-C₆₀heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si and P; a fused ring formed by aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group;a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group, -L′-N(R^(a)) (R^(b)) and the combination thereof.

Preferably, Ar⁶ and Ar⁷ may be independently a C₆-C₁₈ aryl group, afluorenyl group, a C₃-C₁₂ heterocyclic group or -L′-N(R^(a)) (R^(b)) andso on, more preferably, a C₆, C₁₀ or C₁₂ aryl group or a C₁₂heterocyclic group, for example, phenyl, naphthyl, biphenyl, fluorene,spirobifluorene, dibenzothiophene, dibenzofuran or diphenylamine and soon, and each of these may be further substituted with methyl, t-butyl,naphthyl, methoxy, phenyl, pyrimidine or fluorophenyl.

Preferably, Ar⁶ and Ar⁷ may be independently substituted with one ormore substituents selected from the group consisting of deuterium;halogen; a silane group; a siloxane group; a boron group; a germaniumgroup; a cyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.

Further, Ar⁶ and Ar⁷ may be linked together to form a ring.

Further, Ar⁸ may be represented by any one of Formulas 7-a, 7-b and 7-cbelow:

In Formulas 7-a, 7-b and 7-c, R¹ to R³ are each independently selectedfrom the group consisting of hydrogen, deuterium, halogen, a C₆-C₆₀ arylgroup, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₃₀ alkoxy group, a C₆-C₃₀ aryloxy group,-L′-N(R^(a)) (R^(b)) and the combination thereof. q, r and s are each aninteger of 0 to 4, and when q, r and s are each an integer of 2 or more,each of plural R¹s, R^(e)s and R^(a)s may be same or different eachother.

Preferably, R¹ to R³ are each independently hydrogen, a C₆-C₁₂ arylgroup or a C₃-C₁₂ heterocyclic group and so on, more preferably, C₆ arylgroup or a C₁₂ heterocyclic group and so on, and for example, hydrogen,phenyl, carbazole substituted with phenyl and so on.

Preferably, R¹ to R³ may be each independently substituted with one ormore substituents selected from the group consisting of deuterium;halogen; a silane group; a siloxane group; a boron group; a germaniumgroup; a cyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.

Further, adjacent groups among R¹s to R^(a)s may be linked together toform a ring, and the group of R¹ to R³ not forming a ring is the same asdefined in the above, wherein the formed ring may be a monocyclic orpolycyclic ring.

Ar⁹ to Ar¹¹

may be each independently selected from the group consisting of a C₆-C₆₀aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P; a fused ring formed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group,-L′-N(R^(a)) (R^(b)) and the combination thereof.

Preferably, Ar⁹ to Ar¹¹ may be each independently a C₆-C₁₈ aryl group, afluorenyl group or a C₂-C₁₂ heterocyclic group and so on, morepreferably, a C₆, C₁₀ or C₁₂ aryl group, or a C₁₂ heterocyclic group,for example, phenyl, naphthyl, biphenyl, fluorene, spirobifluorene,dibenzothiophene, or dibenzofuran and so on, and each of these may befurther substituted with methyl or phenyl.

Preferably, Ar⁹ to Ar¹¹ may be substituted with one or more substituentsselected from the group consisting of deuterium; halogen; a silanegroup; a siloxane group; a boron group; a germanium group; a cyanogroup; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group; aC₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted with deuterium; afluorenyl group; a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si and P; aC₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group,

L³ and L⁵ may be each independently selected from the group consistingof a C₆-C₆₀ arylene group, a fluorenylene group, a fused ring formed bya C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si and P, and the combination thereof.

Preferably, L³ and L⁵ may be each independently a C₆-C₁₈ arylene group,a fluorenylene group, a C₃-C₁₂ heterocyclic group and so on, morepreferably, a C₁₂ arylene group, for example, biphenyl, fluorine and soon, and each of these may be further substituted with methyl.

L⁴ may be selected from the group consisting of a single bond, a C₆-C₆₀arylene group, a fluorenylene group, a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si and P, and the combination thereof.

Preferably, L⁴ may be a C₆-C₁₈ arylene group or a C₃-C₁₂ heterocyclicgroup and so on, more preferably, a C₆ or C₁₂ arylene group, and forexample, phenyl, biphenyl and so on.

Preferably, when L³ to L⁵ are each an arylene group, a fluorenylenegroup, a heterocyclic group or a fused ring, each of L³ to L⁵ may besubstituted with one or more substituents selected from the groupconsisting of deuterium; halogen; a silane group; a siloxane group; aboron group; a germanium group; a cyano group; a nitro group; a C₁-C₂₀alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀aryl group substituted with deuterium; a fluorenyl group; a C₂-C₂₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si and P; a C₃-C₂₀ cycloalkyl group; aC₇-C₂₀ arylalkyl group; and a C₈-C₂₀ arylalkenyl group.

Specifically, the compound of a hole transport layer represented byFormula 7 may be represented by any one of the following compounds.

In another aspect of the present invention, compound included in theemission-auxiliary layer of the present invention may be the same kindor a mixture of two or more different kinds represented by Formula 1.For example, the emission-auxiliary layer may be formed as same kind ofcompound P-1 among compounds, or as mixture of compounds P-1 and P-2.

In another aspect of the present invention, the present inventionprovides an organic electric element further including a layer toimprove luminescent efficiency which is formed on at least one of thesides the first or second electrodes, which is opposite to the organicmaterial layer.

Hereinafter, synthesis method of the inventive compound according to oneembodiment of the present invention and Preparation method of an organicelectric element will be described in detail by way of example. However,the following examples are only for illustrative purposes and are notintended to limit the scope of the present invention.

SYNTHESIS EXAMPLE I. Synthesis Example of Compounds Represented byFormula 1

The compounds (final products) of the present invention represented byFormula 1 can be synthesized by reaction of Sub 1 and Sub 2 asillustrated in, but not limited to, the following Reaction Scheme 1.

1. Synthesis Example of Compound Sub 1

Compound Sub 1 of the above Reaction Scheme 1 can be synthesized, butnot limited to, by the following Reaction Scheme 2.

Synthesis Examples of compounds comprised in Sub 1 are as followings.

(1) Synthesis Example of Compound Sub 1(1)

1) Synthesis of Compound Sub 1-3(1)

Sub 1-1(1) (0.3 g, 20 mmol), Sub 1-2(1) (6.2 g, 20 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were loaded into a round bottom flask and then thereaction proceeded at 100° C. After the completion of the reaction, areaction product was extracted with CH₂Cl₂ and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundSub 1-3(1) was obtained in the amount of 3.7 g in 76% yield.

2) Synthesis of Compound Sub 1(1)

Sub 1-3(1) (3.7 g, 15.7 mmol), Sub 1-4(1) (4.7 g, 15.7 mmol), Pd₂(dba)₃(0.5 g, 0.5 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol)and toluene (300 mL) were loaded into a round bottom flask and then thereaction proceeded at 100° C. After the completion of the reaction, areaction product was extracted with CH₂Cl₂ and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundSub 1(1) was obtained in the amount of 5.6 g (yield: 78%).

(2) Synthesis Example of Compound Sub 1(11)

1) Synthesis Example of Compound Sub 1-3(1)

Sub 1-1(1) (0.3 g, 20 mmol), Sub 1-2(11) (7.7 g, 20 mmol), Pd₂(dba)₃(0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol)and toluene (300 mL) were loaded into a round bottom flask and then thereaction proceeded at 100° C. After the completion of the reaction, areaction product was extracted with CH₂Cl₂ and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundSub 1-3(11) was obtained in the amount of 4.9 g (yield: 77%).

2) Synthesis Example of Compound Sub 1(11)

Sub 1-3(11) (4.9 g, 15.4 mmol), Sub 1-4(11) (5.9 g, 15.4 mmol),Pd₂(dba)₃ (0.5 g, 0.5 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g,60 mmol) and toluene (300 mL) were loaded into a round bottom flask andthen the reaction proceeded at 100° C. After the completion of thereaction, a reaction product was extracted with CH₂Cl₂ and water. Theorganic layer was dried with MgSO₄ and concentrated. The concentrate wasseparated by silica gel column chromatography and recrystallization,whereby compound Sub 1(11) was obtained in the amount of 7.7 g (yield:80%).

The compounds comprised in Sub 1 may be, but not limited to, thefollowing compounds, and Table 1 below shows FD-MS (FieldDesorption-Mass Spectrometry) data of the compounds.

TABLE 1 compound FD-MS compound FD-MS Sub 1(1) m/z = 473.21(C₃₆H₂₇N =473.61) Sub 1(2) m/z = 523.23(C₄₀H₂₉N = 523.66) Sub 1(3) m/z =673.28(C₅₂H₃₅N = 673.84) Sub 1(4) m/z = 501.25(C₃₈H₃₁N = 501.66) Sub1(5) m/z = 529.28(C₄₀H₃₅N = 529.71) Sub 1(6) m/z = 585.34(C₄₄H₄₃N =585.82) Sub 1(7) m/z = 529.28(C₄₀H₃₅N = 529.71) Sub 1(8) m/z =579.20(C₄₂H₂₉NS = 579.75) Sub 1(9) m/z = 653.24(C₄₈H₃₁NO₂ = 653.77) Sub1(10) m/z = 705.34(C₅₄H₄₃N = 705.93) Sub 1(11) m/z = 625.28(C₄₈H₃₅N =625.80) Sub 1(12) m/z = 599.26(C₄₆H₃₃N = 599.76) Sub 1(13) m/z =626.27(C₄₇H₃₄N₂ = 626.79) Sub 1(14) m/z = 705.25(C₅₂H₃₅NS = 705.91) Sub1(15) m/z = 549.25(C₄₂H₃₁N = 549.70)

2. Synthesis Example of Compound Sub 2

The compounds comprised in Sub 2 of reaction scheme 1 may be, but notlimited to, the following compounds

3. Synthesis Example of Compound Represented by Formula 1 (1) SynthesisExample of Compound P-19

Sub 1(1) (9.5 g, 20 mmol), Sub 2(4) (4.7 g, 20 mmol), Pd₂(dba)₃ (0.5 g,0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were loaded into a round bottom flask and then thereaction proceeded at 100° C. After the completion of the reaction, areaction product was extracted with CH₂Cl₂ and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundP-19 was obtained in the amount of 10.3 g (yield: 82%).

(2) Synthesis Example of Compound P-28

Sub 1(11) (12.5 g, 20 mmol), Sub 2(1) (3.1 g, 20 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were loaded into a round bottom flask and then thereaction proceeded at 100° C. After the completion of the reaction, areaction product was extracted with CH₂Cl₂ and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundP-28 was obtained in the amount of 11.9 g (yield: 85%).

(3) Synthesis Example of Compound P-34

Sub 1(11) (12.5 g, 20 mmol), Sub 2(5) (5.3 g, 20 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were loaded into a round bottom flask and then thereaction proceeded at 100° C. After the completion of the reaction, areaction product was extracted with CH₂Cl₂ and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundP-34 was obtained in the amount of 12.6 g (yield: 78%).

(4) Synthesis Example of Compound P-36

Sub 1(15) (11.0 g, 20 mmol), Sub 2(8) (5.7 g, 20 mmol), Pd₂(dba)₃ (0.5g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) andtoluene (300 mL) were loaded into a round bottom flask and then thereaction proceeded at 100° C. After the completion of the reaction, areaction product was extracted with CH₂Cl₂ and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundP-36 was obtained in the amount of 11.9 g (yield: 78%).

Meanwhile, Table 2 below shows FD-MS data of the final products includedin Formula 1 synthesized according to the above synthesis.

TABLE 2 Compound FD-MS Compound FD-MS P-1 m/z = 549.25(C₄₂H₂₃N = 549.70)P-2 m/z = 599.26(C₄₆H₃₃N = 599.76) P-3 m/z = 749.31(C₅₈H₃₉N = 749.94)P-4 m/z = 577.28(C₄₄H₃₅N = 577.76) P-5 m/z = 605.31(C₄₆H₂₉N = 605.81)P-6 m/z = 661.37(C₅₀H₄₇N = 661.91) P-7 m/z = 605.31(C₄₆H₃₉N = 605.81)P-8 m/z = 655.23(C₄₈H₃₃NS = 655.85) P-9 m/z = 729.27(C₅₄H₃₅NO₂ = 729.86)P-10 m/z = 701.31(C₅₄H₃₉N = 701.89) P-11 m/z = 649.28(C₃₀H₃₅N = 649.82)P-12 m/z = 799.32(C₆₂H₄₁N = 800.00) P-13 m/z = 627.29(C₄₈H₃₇N = 627.81)P-14 m/z = 655.32(C₅₀H₄₁N = 655.87) P-15 m/z = 711.39(C₅₄H₄₂N = 711.97)P-16 m/z = 655.32(C₅₀H₄₁N = 655.87) P-17 m/z = 731.26(C₅₄H₃₇NS = 731.94)P-18 m/z = 731.26(C₅₄H₃₂NS = 731.94) P-19 m/z = 625.28(C₄₈H₃₅N = 625.80)P-20 m/z = 675.29(C₅₂H₃₇N = 675.86) P-21 m/z = 825.34(C₆₄H₄₃N = 826.03)P-22 m/z = 681.34(C₅₂H₄₃N = 681.90) P-23 m/z = 675.29(C₅₂H₃₇N = 675.86)P-24 m/z = 857.40(C₄₀H₅₃N = 858.12) P-25 m/z = 681.34(C₅₂H₄₃N = 681.90)P-26 m/z = 731.26(C₅₄H₃₇NS = 731.94) P-27 m/z = 805.30(C₆₀H₃₉NO₂ =805.96) P-28 m/z = 701.31(C₅₄H₃₉N = 701.89) P-29 m/z = 725.31(C₅₀H₃₉N =725.92) P-30 m/z = 853.37(C₆₆H₄₇N = 854.09) P-31 m/z = 777.34(C₆₀H₄₃N =777.99) P-32 m/z = 702.30(C₅₃H₃₈N₂ = 702.88) P-33 m/z = 831.30(C₆₂H₄₁NS= 832.06) P-34 m/z = 807.30(C₆₀H₄₃NS = 808.04) P-35 m/z = 827.36(C₆₄H₄₅N= 828.05) P-36 m/z = 751.32(C₅₈H₄₁N = 751.95)

II. Synthesis Example of Compound Represented by Formula 7

The compounds (final product 2) of the present invention represented byFormula 7 can be synthesized by reaction of Sub 3 or Sub 4 with Sub 5 asillustrated in, but not limited to, the following Reaction Scheme 3.

1. Synthesis Example of Compound Sub 3

Compound Sub 3 of the above Reaction Scheme 3 can be synthesized asillustrated in, but not limited to, the following Reaction Scheme 4.

Wherein compounds S1 to S7 may be as follows:

In the above Reaction Scheme 4, L corresponds to L³ or L⁵ defined inFormulas 7-a and 7-c.

(1) Synthesis Example of Compound Sub 3-1-1 (L=Biphenyl)

The starting material, 9H-carbazole (50.16 g, 300 mmol), was dissolvedin nitrobenzene (600 ml), 4-bromo-4′-iodo-1,1′-biphenyl (129.2 g, 360mmol), Na₂SO₄ (42.6 g, 300 mmol), K₂CO₃ (41.4 g, 300 mmol) and Cu (5.72g, 90 mmol) were added, and the mixture was stirred at 200° C. Upon thecompletion of the reaction, nitrobenzene from a reaction product wasremoved by distillation, followed by extracting with CH₂Cl₂ and water.The organic layer was dried with MgSO₄ and concentrated. The concentratewas separated by silica gel column chromatography and recrystallization,whereby product was obtained in the amount of 80.05 g (yield: 67%).

(2) Synthesis Example of Compound Sub 3-1-2 (L=9,9-Dimethyl-9H-Fluorene)

Product was obtained in the amount of 88.11 g (yield: 67%) where9H-carbazole (50.16 g, 300 mmol) as a starting material,2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na₂SO₄(42.6 g, 300 mmol), K₂CO₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) andnitrobenzene were used in the same manner as described above for thesynthesis of compound Sub 3-1-1.

(3) Synthesis Example of Compound Sub 3-1-3 (L=9,9-Dimethyl-9H-Fluorene)

Product was obtained in the amount of 92.8 g (yield: 69%) where7H-benzo[c]carbazole (65.18 g, 300 mmol) as a starting material,4-bromo-4′-iodo-1,1′-biphenyl (129.2 g, 360 mmol), Na₂SO₄ (42.6 g, 300mmol), K₂CO₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzenewere used in the same manner as described above for the synthesis ofcompound Sub 3-1-1.

(4) Synthesis Example of Compound Sub 3-1-4 (L=9,9-Dimethyl-9H-Fluorene)

Product was obtained in the amount of 95.24 g (yield: 65%) where7H-benzo[c]carbazole (65.18 g, 300 mmol) as a starting material,2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na₂SO₄(42.6 g, 300 mmol), K₂CO₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) andnitrobenzene were used in the same manner as described above for thesynthesis of compound Sub 3-1-1.

(5) Synthesis Example of Compound Sub 3-1-5 (L=Biphenyl)

Product was obtained in the amount of 80.05 g (yield: 62%) where11H-benzo[a]carbazole (65.18 g, 300 mmol) as a starting material,4-bromo-4′-iodo-1,1′-biphenyl (129.2 g, 360 mmol), Na₂SO₄ (42.6 g, 300mmol), K₂CO₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzenewere used in the same manner as described above for the synthesis ofcompound Sub 3-1-1.

(6) Synthesis Example of Compound Sub 3-1-6 (L=9,9-Dimethyl-9H-Fluorene)

Product was obtained in the amount of 93.78 g (yield: 64%) where5H-benzo[b]carbazole (65.18 g, 300 mmol) as a starting material,2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na₂SO₄(42.6 g, 300 mmol), K₂CO₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) andnitrobenzene were used in the same manner as described above for thesynthesis of compound Sub 3-1-1.

(7) Synthesis Example of Compound Sub 3-1-7 (L=Biphenyl)

Product was obtained in the amount of 98.7 g (yield: 66%) where9H-dibenzo[a,c]carbazole (80.2 g, 300 mmol) as a starting material,4-bromo-4′-iodo-1,1′-biphenyl (129.2 g, 360 mmol), Na₂SO₄ (42.6 g, 300mmol), K₂CO₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzenewere used in the same manner as described above for the synthesis ofcompound Sub 3-1-1.

(8) Synthesis Example of Compound Sub 3-1-8 (L=Biphenyl)

Product was obtained in the amount of 89.2 g (yield: 66%) whereN-phenylnaphthalen-1-amine (65.8 g, 300 mmol) as a starting material,4-bromo-4′-iodo-1,1′-biphenyl (129.2 g, 360 mmol), Na₂SO₄ (42.6 g, 300mmol), K₂CO₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) and nitrobenzenewere used in the same manner as described above for the synthesis ofcompound Sub 3-1-1.

(9) Synthesis Example of Compound Sub 3-1-9 (L=9,9-Dimethyl-9H-Fluorene)

Product was obtained in the amount of 98.5 g (yield: 61%) where7H-dibenzo[c,g]carbazole (80.2 g, 300 mmol) as a starting material,2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (143.7 g, 360 mmol), Na₂SO₄(42.6 g, 300 mmol), K₂CO₃ (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol) andnitrobenzene were used in the same manner as described above for thesynthesis of compound Sub 3-1-1.

2. Synthesis Example of Compound Represented by Sub 4

Compound Sub 4 of the above Reaction Scheme 3 can be synthesized asillustrated in, but not limited to, the following Reaction Scheme 5.

Sub 4

(1) Synthesis Example of Compound M4-2-1 (g=0, Ar⁹=Phenyl)

After dissolving 3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) in DMF980 mL, Bispinacolborate (39.1 g, 154 mmol), PdCl₂(dppf) catalyst (3.43g, 4.2 mmol) and KOAc (41.3 g, 420 mmol) were added in order, and thenthe mixture was stirred for 24 hours, thereby a borate compound wassynthesized. The obtained compound was separated by silica gel columnchromatography, and was then recrystallized, whereby final boratecompound was obtained in the amount of 35.2 g (yield: 68%).

(2) Synthesis Example of Compound M4-2-2 (g=0, Ar⁹=Biphenyl)

Product was obtained in the amount of 40 g (yield: 64%) where3-bromo-9-biphenyl-9H-carbazole (45.1 g, 140 mmol), DMF 980 mL,Bispinacolborate (39.1 g, 154 mmol), PdCl₂(dppf) catalyst (3.43 g, 4.2mmol) and KOAc (41.3 g, 420 mmol) were used in the same manner asdescribed above for the synthesis of compound M4-2-1.

(3) Synthesis Example of Compound Sub 4-1-1 [g=0, Ar⁹=Phenyl,L⁶=Biphenyl (Linear)]

After dissolving M4-2-1 (29.5 g, 80 mmol) in THF 360 mL,4-bromo-4′-iodo-1,1′-biphenyl (30.16 g, 84 mmol), Pd(PPh₃)₄ (2.8 g, 2.4mmol), NaOH (9.6 g, 240 mmol) and water 180 mL were added, and then themixture was refluxed with stirring. Upon the completion of the reaction,a reaction product was extracted with ether and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby finalproduct was obtained in the amount of 26.56 g (yield: 70%).

(4) Synthesis Example of Compound Sub 4-1-2 [g=0, Ar⁹=Phenyl, L⁶=Phenyl]

After dissolving M4-2-1 (29.5 g, 80 mmol) in THF 360 mL,1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh₃)₄ (2.8 g, 2.4 mmol),NaOH (9.6 g, 240 mmol) and water 180 mL were added, and then the mixturewas refluxed with stirring. Upon the completion of the reaction, areaction product was extracted with ether and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundfinal product was obtained in the amount of 22.9 g (yield: 72%).

(5) Synthesis Example of Compound Sub 4-1-3 [g=0, Ar⁹=Phenyl,L⁶=Biphenyl (Non-Linear)]

After dissolving M4-2-1 (29.5 g, 80 mmol) in THF 360 mL,4′-bromo-3-iodo-1,1′-biphenyl (30.16 g, 84 mmol), Pd(PPh₃)₄ (2.8 g, 2.4mmol), NaOH (9.6 g, 240 mmol) and water 180 mL were added, and then themixture was refluxed with stirring. Upon the completion of the reaction,a reaction product was extracted with ether and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundfinal product was obtained in the amount of 24.7 g (yield: 65%).

(6) Synthesis Example of Compound Sub 4-1-4 [g=0, Ar⁹=Biphenyl,L⁶=Biphenyl (Linear)]

After dissolving M4-2-2 (35.63 g, 80 mmol) in THF 360 mL,4-bromo-4′-iodo-1,1′-biphenyl (30.16 g, 84 mmol), Pd(PPh₃)₄ (2.8 g, 2.4mmol), NaOH (9.6 g, 240 mmol) and water 180 mL were added, and then themixture was refluxed with stirring. Upon the completion of the reaction,a reaction product was extracted with ether and water. The organic layerwas dried with MgSO₄ and concentrated. The concentrate was separated bysilica gel column chromatography and recrystallization, whereby compoundfinal product was obtained in the amount of 29.51 g (yield: 67%).

3. Synthesis Example of Compound Sub 5

Compound Sub 5 of the above Reaction Scheme 3 can be synthesized asillustrated in, but not limited to, the following Reaction Scheme 6.

(1) Synthesis Example of Compound Sub 5-28

After dissolving 4-bromo-1,1′-biphenyl (37.88 g, 162.5 mmol) in toluene(2200 mL) in a round bottom flask, [1,1′-biphenyl]-4-amine (25 g, 147.7mmol), Pd₂(dba)₃ (6.76 g, 7.4 mmol), P(t-Bu)₃ (3 g, 14.8 mmol) andNaOt-Bu (66.62 g, 693.2 mmol) were added in order, and then the mixturewas stirred at 100° C. Upon the completion of the reaction, a reactionproduct was extracted with ether and water. The organic layer was driedwith MgSO₄ and concentrated. The concentrate was separated by silica gelcolumn chromatography and recrystallization, whereby a product wasobtained in the amount of 28 g (yield: 77%).

Meanwhile, the compounds comprised in Sub 5 may be, but not limited to,the following compounds, and Table 3 below shows FD-MS (FieldDesorption-Mass Spectrometry) data of the compounds.

TABLE 3 Compound FD-MS Compound FD-MS Sub 5-1 m/z = 169.09(C₁₂H₁₁N =169.22) Sub 5-2 m/z = 219.10(C₁₆H₁₃N = 219.28) Sub 5-3 m/z =219.10(C₁₆H₁₃N = 219.28) Sub 5-4 m/z = 245.12(C₁₈H₁₅N = 245.32) Sub 5-5m/z = 170.08(C₁₁H₁₀N₂ = 170.21) Sub 5-6 m/z = 199.10(C₁₀H₁₃NO = 199.25)Sub 5-7 m/z = 225.15(C₁₆H₁₀N = 225.33) Sub 5-8 m/z = 285.15(C₂₁H₁₉N =285.38) Sub 5-9 m/z = 409.18(C₃₁H₂₃N = 409.52) Sub 5-10 m/z =407.17(C₃₁H₂₃N = 407.51) Sub 5-11 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub5-12 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 5-13 m/z = 295.14(C₂₂H₁₇N =295.38) Sub 5-14 m/z = 220.10(C₁₅H₁₂N₂ = 220.27) Sub 5-15 m/z =249.12(C₁₇H₁₂NO = 249.31) Sub 5-16 m/z = 275.17(C₂₀H₂₁N = 275.39) Sub5-17 m/z = 335.17(C₂₅H₂₃N = 335.44) Sub 5-18 m/z = 459.20(C₃₃H₂₅N =459.58) Sub 5-19 m/z = 457.18(C₃₅H₂₃N = 457.56) Sub 5-20 m/z =269.12(C₂₀H₁₅N = 269.34) Sub 5-21 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub5-22 m/z = 220.10(C₁₅H₂N₂ = 220.27) Sub 5-23 m/z = 249.12(C₁₇H₁₉NO =249.31) Sub 5-24 m/z = 275.17(C₂₀H₂₁N = 275.39) Sub 5-25 m/z =335.17(C₂₅H₂₁N = 335.44) Sub 5-26 m/z = 459.20(C₃₅H₂₅N = 459.28) Sub5-27 m/z = 457.18(C₃₅H₂₃N = 457.56) Sub 5-28 m/z = 321.15(C₂₄H₁₉N =321.41) Sub 5-29 m/z = 246.12(C₁₇H₁₄N₂ = 246.31) Sub 5-30 m/z =275.13(C₁₉H₁₇NO = 275.34) Sub 5-31 m/z = 301.18(C₂₂H₂₃N = 301.42) Sub5-32 m/z = 361.18(C₂₇H₂₃N = 361.48) Sub 5-33 m/z = 485.21(C₃₇H₂₇N =485.62) Sub 5-34 m/z = 483.20(C₃₇H₂₅N = 483.60) Sub 5-35 m/z =171.08(C₁₀H₀₉N₃ = 171.20) Sub 5-36 m/z = 200.09(C₁₂H₁₂N₂O = 200.24) Sub5-37 m/z = 226.15(C₁₅H₁₈N₂ = 226.32) Sub 5-38 m/z = 286.15(C₂₀H₁₈N₂ =286.37) Sub 5-39 m/z = 410.18(C₃₀H₂₂N₂ = 410.51) Sub 5-40 m/z =408.16(C₃₀H₂₀N₂ = 408.49) Sub 5-41 m/z = 229.11(C₁₄H₁₉NO₂ = 229.27) Sub5-42 m/z = 255.16(C₁₇H₂₃NO = 255.35) Sub 5-43 m/z = 315.16(C₂₂H₂₃NO =315.41) Sub 5-44 m/z = 439.19(C₃₂H₂₅NO = 439.55) Sub 5-45 m/z =437.18(C₃₂H₂₃NO = 437.53) Sub 5-46 m/z = 281.21(C₂₀H₂₇N = 281.44) Sub5-47 m/z = 341.21(C₂₅H₂₇N = 341.49) Sub 5-48 m/z = 465.25(C₃₅H₃₁N =465.63) Sub 5-49 m/z = 463.23(C₃₅H₂₉N = 463.61) Sub 5-50 m/z =401.21(C₃₀H₂₇N = 401.54) Sub 5-51 m/z = 525.25(C₄₀H₃₁N = 525.68) Sub5-52 m/z = 523.23(C₆₀H₂₉N = 523.66)

4. Synthesis Example of Compound Represented by Formula 7 (1) SynthesisExample of Compound 1-17

After dissolving 9-(4′-bromo-[1,1′-biphenyl]-4-yl)-9H-carbazole(9.6 g,24 mmol) in toluene, di([1,1′-biphenyl]-4-yl)amine(6.4 g, 20 mmol),Pd₂(dba)₃ (0.05 eq.), PPh₃ (0.1 eq.) and NaOt-Bu (3 eq.) were added, andthen the mixture was refluxed with stirring at 100□ for 24 hours. Uponthe completion of the reaction, a reaction product was extracted withether and water. The organic layer was dried with MgSO₄ andconcentrated. The concentrate was separated by silica gel columnchromatography and recrystallization, whereby a final product wasobtained in the amount of 12.9 g (yield: 84%).

(2) Synthesis Example of Compound 1-32

After dissolving 3-(4-bromophenyl)-9-phenyl-9H-carbazole (9.6 g, 24mmol) in toluene,N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20mmol), Pd₂(dba)₃ (0.05 eq.), PPh₃ (0.1 eq.) and NaOt-Bu (3 eq.) wereadded, and then the mixture was refluxed with stirring at 100□ for 24hours. Upon the completion of the reaction, a reaction product wasextracted with ether and water. The organic layer was dried with MgSO₄and concentrated. The concentrate was separated by silica gel columnchromatography and recrystallization, whereby a final product wasobtained in the amount of 13.8 g (yield: 85%).

(3) Synthesis Example of Compound 1-61

After dissolvingN-(4′-bromo-[1,1′-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (10.8 g, 24mmol) in toluene, N-phenylnaphthalen-1-amine (4.4 g, 20 mmol), Pd₂(dba)₃(0.05 eq.), PPh₃ (0.1 eq.), NaOt-Bu (3 eq.) were added, and then themixture was refluxed with stirring at 100□ for 24 hours. Upon thecompletion of the reaction, a reaction product was extracted with etherand water. The organic layer was dried with MgSO₄ and concentrated. Theconcentrate was separated by silica gel column chromatography andrecrystallization, whereby a final product was obtained in the amount of11.4 g (yield: 81%).

Meanwhile, Table 4 below shows FD-MS data of final products included inFormula 7 synthesized according to the above synthesis.

TABLE 4 Compound FD-MS Compound FD-MS 1-17 m/z = 638.27 (C₄₈H₃₄N₂ =638.80) 1-20 m/z = 678.30 (C₅₁H₃₈N₂ = 678.86) 1-21 m/z = 802.33(C₆₁H₄₂N₂ = 803.00) 1-22 m/z = 800.30 (C₆₁H₄₀N₂ = 800.98) 1-32 m/z =678.30 (C₅₁H₃₈N₂ = 678.86) 1-33 m/z = 802.33 (C₆₁H₄₂N₂ = 803.00) 1-34m/z = 800.32 (C₆₁H₄₀N₂ = 800.98) 1-43 m/z = 714.30 (C₅₄H₃₈N₂ = 714.89)1-44 m/z = 754.33 (C₅₇H₄₂N₂ = 754.96) 1-45 m/z = 878.37 (C₆₇H₄₆N₂ =879.10) 1-46 m/z = 876.35 (C₆₇H₄₄N₂ = 877.08) 1-47 m/z = 744.26(C₅₄H₃₆N₂S = 744.94) 1-52 m/z = 826.33 (C₆₃H₄₂N₂ = 827.02) 1-53 m/z =824.32 (C₆₃H₄₀N₂ = 825.01) 1-54 m/z = 688.29 (C₅₂H₃₆N₂ = 688.86) 1-55m/z = 728.32 (C₅₅H₄₀N₂ = 728.92) 1-57 m/z = 778.33 (C₅₉H₄₂N₂ = 778.98)1-58 m/z = 902.37 (C₆₉H₄₆N₂ = 903.12) 1-59 m/z = 900.53 (C₆₉H₄₄N₂ =901.10) 1-60 m/z = 538.24 (C₄₀H₃₀N₂ = 538.68) 1-61 m/z = 588.26(C₄₄H₈₂N₂ = 588.74) 1-62 m/z = 586.26 (C₄₄H₃₂N₂ = 588.74) 1-63 m/z =614.27 (C₄₀H₃₄N₂ = 614.78)

Fabrication and Evaluation of Organic Electronic Element

[Example (1)] Green OLED

First, an ITO layer (anode) was formed on a glass substrate, and thenN¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter, “2-TNATA”) was vacuum-deposited on the ITO layer to form ahole injection layer with a thickness of 60 nm.

Subsequently, compound 1-17 of the present invention as compound of ahole transport layer was vacuum-deposited with a thickness of 60 nm onthe hole injection layer to form a hole transport layer.

Next, compound P-1 as compound of an emission-auxiliary layer wasvacuum-deposited with a thickness of 20 nm on the hole transport layerto form an emission-auxiliary layer.

Next, a light emitting layer with a thickness of 30 nm was formed on theemission-auxiliary layer by using 4,4′-N,N′-dicarbazole-biphenyl(hereinafter, “CBP”) as host material and tris(2-phenylpyridine)-iridium(hereinafter, “Ir(ppy)₃)”) as dopant material in a weight ratio of 95:5.

Next, a film of((1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film oftris(8-quinolinolato)aluminum (hereinafter, “Alq₃”) was formed with athickness of 40 nm to form an electron transport layer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

[Example (2)] to [Example (36)] Green OLED

The OLEDs were each manufactured in the same manner as described inExample (1) except that any one of the compounds P-2 to P-36 listed inTable 5 below was used as an emission-auxiliary layer material, insteadof the inventive compound P-1.

[Example (37)] to [Example (72)] Green OLED

The OLEDs were each manufactured in the same manner as described inExample (1) except that compound 1-32 instead of the inventive compound1-17 was used as a hole transport layer material and any one ofcompounds P-1 to P-36 listed in Table below was used as anemission-auxiliary layer material instead of the inventive compound P-1.

[Example (73)] to [Example (108)] Green OLED

The OLEDs were each manufactured in the same manner as described inExample (1) except that compound 1-61 instead of the inventive compound1-17 was used as a hole transport layer material and any one of the P-1to P-36 listed in Table 5 below was used as an emission-auxiliary layermaterial instead of the inventive compound P-1.

[Comparative Example (1)] to [Example (3)] Green OLED

The OLEDs were each manufactured in the same manner as described inExample (1) except that any one of compounds 1-17, 1-32 and 1-61 wasused as a hole transport layer material and an emission-auxiliary layerwas not formed.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough the Examples (1) to (108) and the Comparative Examples (1) to(3), and electro-luminescence (EL) characteristics of the OLED weremeasured by PR-650 (Photoresearch). Also, T95 life span was measured bylife span measuring equipment (Mcscience) at reference brightness of5000 cd/m². Evaluation results are given in the Table 5 below.

TABLE 5 Current Voltage Density Brightness Efficiency Lifetime HTL com.EAL com. (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp.Ex(1) Com.(1-17) — 6.316.1 5000.0 31.0 87.9 comp.Ex(2) Com.(1-32) — 5.9 13.2 5000.0 38.0 78.4comp.Ex(3) Com.(1-61) — 6.5 21.7 5000.0 23.0 61.9 Ex.(1) Com.(1-17)Com.(P-1) 6.3 10.2 5000.0 49.2 137.9 Ex.(2) Com.(1-17) Com.(P-2) 6.410.6 5000.0 47.4 149.3 Ex.(3) Com.(1-17) Com.(P-3) 6.4 11.0 5000.0 45.4107.1 Ex.(4) Com.(1-17) Com.(P-4) 6.3 12.2 5000.0 41.0 135.9 Ex.(5)Com.(1-17) Com.(P-5) 6.4 11.1 5000.0 45.0 96.3 Ex.(6) Com.(1-17)Com.(P-6) 6.4 11.5 5000.0 43.3 138.4 Ex.(7) Com.(1-17) Com.(P-7) 6.411.9 5000.0 42.1 119.9 Ex.(8) Com.(1-17) Com.(P-8) 6.3 12.1 5000.0 41.2108.3 Ex.(9) Com.(1-17) Com.(P-9) 6.2 11.3 5000.0 44.4 100.6 Ex.(10)Com.(1-17) Com.(P-10) 6.5 10.8 5000.0 46.1 147.6 Ex.(11) Com.(1-17)Com.(P-11) 6.4 11.1 5000.0 45.2 98.2 Ex.(12) Com.(1-17) Com.(P-12) 6.310.7 5000.0 46.6 130.4 Ex.(13) Com.(1-17) Com.(P-13) 6.3 10.2 5000.048.9 141.2 Ex.(14) Com.(1-17) Com.(P-14) 6.3 11.7 5000.0 42.7 100.9Ex.(15) Com.(1-17) Com.(P-15) 6.4 11.6 5000.0 43.2 138.7 Ex.(16)Com.(1-17) Com.(P-16) 6.3 11.8 5000.0 42.2 132.7 Ex.(17) Com.(1-17)Com.(P-17) 6.3 11.1 5000.0 45.0 115.1 Ex.(18) Com.(1-17) Com.(P-18) 6.412.1 5000.0 41.5 127.6 Ex.(19) Com.(1-17) Com.(P-19) 6.2 10.0 5000.050.0 145.0 Ex.(20) Com.(1-17) Com.(P-20) 6.5 10.1 5000.0 49.5 104.1Ex.(21) Com.(1-17) Com.(P-21) 6.3 10.5 5000.0 47.5 129.8 Ex.(22)Com.(1-17) Com.(P-22) 6.5 11.2 5000.0 44.5 131.3 Ex.(23) Com.(1-17)Com.(P-23) 6.3 10.4 5000.0 47.9 126.3 Ex.(24) Com.(1-17) Com.(P-24) 6.511.2 5000.0 44.7 97.4 Ex.(25) Com.(1-17) Com.(P-25) 6.4 11.5 5000.0 43.6144.2 Ex.(26) Com.(1-17) Com.(P-26) 6.5 12.5 5000.0 40.2 100.7 Ex.(27)Com.(1-17) Com.(P-27) 6.3 11.5 5000.0 43.4 92.9 Ex.(28) Com.(1-17)Com.(P-28) 6.3 10.9 5000.0 45.9 133.5 Ex.(29) Com.(1-17) Com.(P-29) 6.411.1 5000.0 45.1 131.3 Ex.(30) Com.(1-17) Com.(P-30) 6.4 10.1 5000.049.6 142.0 Ex.(31) Com.(1-17) Com.(P-31) 6.5 10.4 5000.0 47.9 132.9Ex.(32) Com.(1-17) Com.(P-32) 6.5 11.2 5000.0 44.5 91.0 Ex.(33)Com.(1-17) Com.(P-33) 6.5 12.2 5000.0 40.9 139.0 Ex.(34) Com.(1-17)Com.(P-34) 6.4 11.8 5000.0 42.3 94.5 Ex.(35) Com.(1-17) Com.(P-35) 6.410.5 5000.0 47.7 147.5 Ex.(36) Com.(1-17) Com.(P-36) 6.4 10.8 5000.046.5 124.4 Ex.(37) Com.(1-32) Com.(P-1) 6.0 9.8 5000.0 51.1 146.2Ex.(38) Com.(1-32) Com.(P-2) 5.9 9.6 5000.0 52.3 132.0 Ex.(39)Com.(1-32) Com.(P-3) 5.9 10.0 5000.0 50.2 124.6 Ex.(40) Com.(1-32)Com.(P-4) 6.0 11.0 5000.0 45.5 98.2 Ex.(41) Com.(1-32) Com.(P-5) 5.810.3 5000.0 48.6 130.9 Ex.(42) Com.(1-32) Com.(P-6) 5.8 11.1 5000.0 45.2105.8 Ex.(43) Com.(1-32) Com.(P-7) 6.0 10.9 5000.0 45.7 111.4 Ex.(44)Com.(1-32) Com.(P-8) 6.0 10.6 5000.0 47.2 147.1 Ex.(45) Com.(1-32)Com.(P-9) 5.9 10.3 5000.0 48.7 97.8 Ex.(46) Com.(1-32) Com.(P-10) 6.09.9 5000.0 50.4 138.0 Ex.(47) Com.(1-32) Com.(P-11) 6.0 9.8 5000.0 50.9125.8 Ex.(48) Com.(1-32) Com.(P-12) 5.9 9.8 5000.0 51.1 136.9 Ex.(49)Com.(1-32) Com.(P-13) 5.8 10.4 5000.0 48.2 144.7 Ex.(50) Com.(1-32)Com.(P-14) 5.9 10.7 5000.0 46.6 119.2 Ex.(51) Com.(1-32) Com.(P-15) 6.010.3 5000.0 48.4 129.8 Ex.(52) Com.(1-32) Com.(P-16) 5.9 10.2 5000.049.2 128.8 Ex.(53) Com.(1-32) Com.(P-17) 6.0 10.8 5000.0 46.4 104.0Ex.(54) Com.(1-32) Com.(P-18) 5.9 10.7 5000.0 46.9 111.8 Ex.(55)Com.(1-32) Com.(P-19) 5.9 8.9 5000.0 56.3 151.0 Ex.(56) Com.(1-32)Com.(P-20) 5.8 9.3 5000.0 53.7 91.6 Ex.(57) Com.(1-32) Com.(P-21) 5.89.9 5000.0 50.4 134.6 Ex.(58) Com.(1-32) Com.(P-22) 6.0 10.0 5000.0 50.098.2 Ex.(59) Com.(1-32) Com.(P-23) 5.8 9.1 5000.0 54.7 97.9 Ex.(60)Com.(1-32) Com.(P-24) 6.0 10.9 5000.0 45.7 96.3 Ex.(61) Com.(1-32)Com.(P-25) 5.9 10.1 5000.0 49.5 119.9 Ex.(62) Com.(1-32) Com.(P-26) 6.010.1 5000.0 49.4 94.4 Ex.(63) Com.(1-32) Com.(P-27) 5.8 10.5 5000.0 47.8121.8 Ex.(64) Com.(1-32) Com.(P-28) 5.9 9.3 5000.0 53.7 137.4 Ex.(65)Com.(1-32) Com.(P-29) 5.9 9.1 5000.0 54.7 145.9 Ex.(66) Com.(1-32)Com.(P-30) 5.8 9.1 5000.0 54.8 94.7 Ex.(67) Com.(1-32) Com.(P-31) 6.09.9 5000.0 50.3 124.5 Ex.(68) Com.(1-32) Com.(P-32) 5.9 10.8 5000.0 46.3120.1 Ex.(69) Com.(1-32) Com.(P-33) 5.8 10.5 5000.0 47.6 95.4 Ex.(70)Com.(1-32) Com.(P-34) 5.8 11.1 5000.0 45.2 96.6 Ex.(71) Com.(1-32)Com.(P-35) 5.9 9.3 5000.0 53.9 93.0 Ex.(72) Com.(1-32) Com.(P-36) 5.89.3 5000.0 53.8 144.8 Ex.(73) Com.(1-61) Com.(P-1) 6.4 12.9 5000.0 38.7110.5 Ex.(74) Com.(1-61) Com.(P-2) 6.4 12.8 5000.0 39.0 117.3 Ex.(75)Com.(1-61) Com.(P-3) 6.5 13.1 5000.0 38.2 111.7 Ex.(76) Com.(1-61)Com.(P-4) 6.6 14.4 5000.0 34.8 100.3 Ex.(77) Com.(1-61) Com.(P-5) 6.414.9 5000.0 33.5 107.2 Ex.(78) Com.(1-61) Com.(P-6) 6.6 14.5 5000.0 34.6111.5 Ex.(79) Com.(1-61) Com.(P-7) 6.6 14.9 5000.0 33.5 90.3 Ex.(80)Com.(1-61) Com.(P-8) 6.5 14.8 5000.0 33.8 113.8 Ex.(81) Com.(1-61)Com.(P-9) 6.5 14.9 5000.0 33.5 115.4 Ex.(82) Com.(1-61) Com.(P-10) 6.612.6 5000.0 39.7 99.5 Ex.(83) Com.(1-61) Com.(P-11) 6.7 14.3 5000.0 35.1118.9 Ex.(84) Com.(1-61) Com.(P-12) 6.5 13.4 5000.0 37.4 92.1 Ex.(85)Com.(1-61) Com.(P-13) 6.5 15.0 5000.0 33.3 116.9 Ex.(86) Com.(1-61)Com.(P-14) 6.5 14.7 5000.0 34.0 118.8 Ex.(87) Com.(1-61) Com.(P-15) 6.515.1 5000.0 33.1 97.2 Ex.(88) Com.(1-61) Com.(P-16) 6.6 14.7 5000.0 34.0114.3 Ex.(89) Com.(1-61) Com.(P-17) 6.6 14.7 5000.0 34.1 104.0 Ex.(90)Com.(1-61) Com.(P-18) 6.6 14.8 5000.0 33.7 116.5 Ex.(91) Com.(1-61)Com.(P-19) 6.6 11.6 5000.0 43.0 124.0 Ex.(92) Com.(1-61) Com.(P-20) 6.413.1 5000.0 38.1 105.3 Ex.(93) Com.(1-61) Com.(P-21) 6.6 13.9 5000.035.9 95.4 Ex.(94) Com.(1-61) Com.(P-22) 6.5 14.5 5000.0 34.6 114.4Ex.(95) Com.(1-61) Com.(P-23) 6.7 14.1 5000.0 35.4 116.2 Ex.(96)Com.(1-61) Com.(P-24) 6.4 14.9 5000.0 33.7 100.0 Ex.(97) Com.(1-61)Com.(P-25) 6.5 15.1 5000.0 33.1 110.3 Ex.(98) Com.(1-61) Com.(P-26) 6.615.1 5000.0 33.2 97.2 Ex.(99) Com.(1-61) Com.(P-27) 6.6 14.4 5000.0 34.6109.6 Ex.(100) Com.(1-61) Com.(P-28) 6.5 12.6 5000.0 39.6 97.1 Ex.(101)Com.(1-61) Com.(P-29) 6.6 13.3 5000.0 37.7 98.7 Ex.(102) Com.(1-61)Com.(P-30) 6.7 13.7 5000.0 36.4 94.4 Ex.(103) Com.(1-61) Com.(P-31) 6.513.4 5000.0 37.5 116.3 Ex.(104) Com.(1-61) Com.(P-32) 6.6 15.1 5000.033.0 90.9 Ex.(105) Com.(1-61) Com.(P-33) 6.6 15.1 5000.0 33.1 96.1Ex.(106) Com.(1-61) Com.(P-34) 6.6 14.4 5000.0 34.8 111.8 Ex.(107)Com.(1-61) Com.(P-35) 6.5 12.6 5000.0 39.7 108.7 Ex.(108) Com.(1-61)Com.(P-36) 6.7 12.8 5000.0 39.1 118.4

[Example (109)] Blue OLED

First, an ITO layer (anode) was formed on a glass substrate, and then2-TNATA was vacuum-deposited on the ITO layer to form a hole injectionlayer with a thickness of 60 nm.

Subsequently, compound P1-17 of the present invention as compound of ahole transport layer was vacuum-deposited with a thickness of 60 nm onthe hole injection layer to form a hole transport layer.

Next, compound P-1 as compound of an emission-auxiliary layer wasvacuum-deposited with a thickness of 20 nm on the hole transport layerto form an emission-auxiliary layer.

Next, a light emitting layer with a thickness of 30 nm was formed on theemission-auxiliary layer by using 9,10-di(naphthalen-2-yl)anthracene ashost material and BD-052X(Idemitsu kosan) as dopant material in a weightratio of 96:4.

Next, a film of BAlq was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film ofAlq₃ was formed with a thickness of 40 nm to form an electron transportlayer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

[Example (110)] to [Example (124)] Blue OLED

The OLEDs were each manufactured in the same manner as described inExample (109) except that any one of the P-2, P-3, P-10 to P-12, P-19 toP-21, P-23, P-28 to P-31, P-35 and P-36 listed in Table 6 below was usedas an emission-auxiliary layer material, instead of the inventivecompound P-1.

[Example (125)] to [Example (140)] Blue OLED

The OLEDs were each manufactured in the same manner as described inExample (109) except that compound 1-32 instead of the inventivecompound 1-17 was used as a hole transport layer material and any one ofthe P-1 to P-3, P-10 to P-12, P-19 to P-21, P-23, P-28 to P-31, P-35 andP-36 listed in Table below was used as an emission-auxiliary layermaterial instead of the inventive compound P-1.

[Example (141)] to [Example (156)] Blue OLED

The OLEDs were each manufactured in the same manner as described inExample (109) except that compound 1-61 instead of the inventivecompound 1-17 was used as a hole transport layer material and any one ofthe P-1 to P-3, P-10 to P-12, P-19 to P-21, P-23, P-28 to P-31, P-35 andP-36 listed in Table below was used as an emission-auxiliary layermaterial instead of the inventive compound P-1.

[Comparative Example (4)] to [Example (6)] Blue OLED

The OLEDs were each manufactured in the same manner as described inExample (109) except that any one of compounds 1-17, 1-32 and 1-61 wasused as a hole transport layer material and an emission-auxiliary layerwas not formed.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough the Examples (109) to (156) and the Comparative Examples (4) to(6), and electro-luminescence (EL) characteristics of the OLED weremeasured by PR-650 (Photoresearch). Also, T95 life span was measured bylife span measuring equipment (Mcscience) at reference brightness of5000 cd/m². Evaluation results are given in the Table 6 below.

TABLE 6 Current Voltage Density Brightness Efficiency Lifetime HTL com.EAL com. (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp.Ex(4) Com.(1-17) — 4.811.6 500.0 4.3 91.7 comp.Ex(5) Com.(1-32) — 4.3 9.6 500.0 5.2 93.7comp.Ex(6) Com.(1-61) — 5.3 13.5 500.0 3.7 85.3 Ex.(109) Com.(1-17)Com.(P-1) 4.9 9.0 500.0 5.5 112.2 Ex.(110) Com.(1-17) Com.(P-2) 4.8 9.3500.0 5.4 131.3 Ex.(111) Com.(1-17) Com.(P-3) 4.8 8.4 500.0 6.0 120.0Ex.(112) Com.(1-17) Com.(P-10) 4.7 9.4 500.0 5.3 136.8 Ex.(113)Com.(1-17) Com.(P-11) 4.8 7.9 500.0 6.3 123.2 Ex.(114) Com.(1-17)Com.(P-12) 4.7 8.9 500.0 5.6 125.5 Ex.(115) Com.(1-17) Com.(P-19) 4.76.7 500.0 7.5 149.9 Ex.(116) Com.(1-17) Com.(P-20) 4.9 7.5 500.0 6.6115.8 Ex.(117) Com.(1-17) Com.(P-21) 4.8 8.7 500.0 5.8 138.5 Ex.(118)Com.(1-17) Com.(P-23) 4.7 9.8 500.0 5.1 110.0 Ex.(119) Com.(1-17)Com.(P-28) 4.8 9.2 500.0 5.4 104.9 Ex.(120) Com.(1-17) Com.(P-29) 4.89.8 500.0 5.1 109.0 Ex.(121) Com.(1-17) Com.(P-30) 4.9 9.8 500.0 5.1120.5 Ex.(122) Com.(1-17) Com.(P-31) 4.8 7.6 500.0 6.6 96.2 Ex.(123)Com.(1-17) Com.(P-35) 4.7 7.6 500.0 6.6 104.1 Ex.(124) Com.(1-17)Com.(P-36) 4.9 9.5 500.0 5.3 109.1 Ex.(125) Com.(1-32) Com.(P-1) 4.4 7.7500.0 6.5 113.8 Ex.(126) Com.(1-32) Com.(P-2) 4.3 7.3 500.0 6.8 114.1Ex.(127) Com.(1-32) Com.(P-3) 4.2 6.5 500.0 7.6 139.6 Ex.(128)Com.(1-32) Com.(P-10) 4.4 6.6 500.0 7.5 147.4 Ex.(129) Com.(1-32)Com.(P-11) 4.4 6.6 500.0 7.6 92.0 Ex.(130) Com.(1-32) Com.(P-12) 4.4 7.2500.0 6.9 122.3 Ex.(131) Com.(1-32) Com.(P-19) 4.4 6.2 500.0 8.1 148.3Ex.(132) Com.(1-32) Com.(P-20) 4.3 6.3 500.0 7.9 93.6 Ex.(133)Com.(1-32) Com.(P-21) 4.5 7.2 500.0 6.9 146.8 Ex.(134) Com.(1-32)Com.(P-23) 4.5 7.6 500.0 6.6 106.1 Ex.(135) Com.(1-32) Com.(P-28) 4.36.9 500.0 7.2 124.2 Ex.(136) Com.(1-32) Com.(P-29) 4.3 6.3 500.0 8.0128.7 Ex.(137) Com.(1-32) Com.(P-30) 4.3 6.9 500.0 7.2 138.1 Ex.(138)Com.(1-32) Com.(P-31) 4.4 7.0 500.0 7.1 96.4 Ex.(139) Com.(1-32)Com.(P-35) 4.3 6.7 500.0 7.5 142.1 Ex.(140) Com.(1-32) Com.(P-36) 4.27.3 500.0 6.9 131.9 Ex.(141) Com.(1-61) Com.(P-1) 5.2 9.5 500.0 5.3 99.3Ex.(142) Com.(1-61) Com.(P-2) 5.3 10.3 500.0 4.8 117.9 Ex.(143)Com.(1-61) Com.(P-3) 5.3 8.5 500.0 5.9 126.2 Ex.(144) Com.(1-61)Com.(P-10) 5.3 10.5 500.0 4.8 118.9 Ex.(145) Com.(1-61) Com.(P-11) 5.29.6 500.0 5.2 124.5 Ex.(146) Com.(1-61) Com.(P-12) 5.3 9.7 500.0 5.2106.2 Ex.(147) Com.(1-61) Com.(P-19) 5.3 7.9 500.0 6.3 142.1 Ex.(148)Com.(1-61) Com.(P-20) 5.3 9.8 500.0 5.1 146.6 Ex.(149) Com.(1-61)Com.(P-21) 5.3 11.0 500.0 4.5 92.7 Ex.(150) Com.(1-61) Com.(P-23) 5.49.2 500.0 5.5 123.1 Ex.(151) Com.(1-61) Com.(P-28) 5.3 8.8 500.0 5.7144.9 Ex.(152) Com.(1-61) Com.(P-29) 5.2 9.2 500.0 5.4 141.6 Ex.(153)Com.(1-61) Com.(P-30) 5.3 8.6 500.0 5.8 118.5 Ex.(154) Com.(1-61)Com.(P-31) 5.3 8.5 500.0 5.9 123.7 Ex.(155) Com.(1-61) Com.(P-35) 5.38.6 500.0 5.8 120.4 Ex.(156) Com.(1-61) Com.(P-36) 5.5 9.5 500.0 5.2107.4

It can be seen from the results in Tables 5 and 6 above, that Examplesof the present employing the inventive compounds represented by Formula7 as a hole transport layer material and the inventive compoundsrepresented by Formula 1 as an emission-auxiliary layer material showeda similar or slightly increased driving voltage, predominantly improvedluminescent efficiency and lifespan, compared to Comparative examplesemploying the inventive compounds represented by Formula 7 as a holetransport layer material and not forming an emission-auxiliary layer.

Further, the electrical properties of the OLED employing compound 1-32among compounds 1-17, 1-32 and 1-61 represented by Formula 7 was themost excellent, when compound represented by Formula 1 was employed asan emission-auxiliary layer material or an emission-auxiliary layer wasnot formed.

This may be caused by the fact that when compound of the presentinvention is used as a material of an emission-auxiliary layer, anappropriate amount of holes can be efficiently transferred into a lightemitting layer from a hole transport layer due to deeper HOMO energylevels which is unique characteristics of the inventive compound, andthus a charge balance of the holes and electrons keeps in the lightemitting layer and high T1 prevents electrons from transferring from thelight emitting layer resulting in improving color purity and maximizingan efficiency by emitting in interface of a hole transport layer.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

1. An organic electric element, comprising: a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode and comprising at least anemission-auxiliary layer and a hole transport layer, wherein theemission-auxiliary layer comprises compound represented by Formula 1below,

wherein, Ar¹ to Ar⁵ are each independently selected from the groupconsisting of a C₆-C₂₄ aryl group; a fluorenyl group; a C₂-C₂₅heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si and P; a fused ring formed by a C₃-C₂₄aliphatic ring and a C₆-C₂₄ aromatic ring; a C₁-C₂₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group and the combination thereof, L¹ and L² are eachindependently selected from the group consisting of a single bond, aC₆-C₂₄ arylene group, a fluorenylene group, a C₂-C₂₄ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, a fused ring formed by a C₃-C₂₄ aliphatic ring and aC₆-C₂₄ aromatic ring and the combination thereof, when Ar¹ to Ar⁵ areeach independently an aryl group, a fluorenyl group, a heterocyclicgroup, a fused ring, an alkyl group, an alkenyl group, an alkynyl group,an alkoxy group, or an aryloxy group, each of Ar¹ to Ar^(y) may besubstituted with one or more substituents selected from the groupconsisting of deuterium; halogen; a silane group; a siloxane group; aboron group; a germanium group; a cyano group; a nitro group; a C₁-C₂₀alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀aryl group substituted with deuterium; a fluorenyl group; a C₂-C₂₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a C₃-C₂₀ cycloalkyl group; aC₇-C₂₀ arylalkyl group; and a C₈-C₂₀ arylalkenyl group, and when L¹ andL² are each independently an arylene group, a fluorenylene group, aheterocyclic group or a fused ring, each of L¹ and L² may be substitutedwith one or more substituents selected from the group consisting ofdeuterium; halogen; a silane group; a siloxane group; a boron group; agermanium group; a cyano group; a nitro group; a C₁-C₂₀ alkylthio group;a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; aC₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl groupsubstituted with deuterium; a fluorenyl group; a C₂-C₂₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀arylalkyl group; and a C₈-C₂₀ arylalkenyl group.
 2. The organic electricelement of claim 1, wherein Formula 1 is represented by one of Formulas2 to 6 below:

in formulas 2 to 6, Ar¹ to Ar⁵, L¹ and L² are each the same as definedin claim
 1. 3. The organic electric element of claim 1, Ar¹ to Ar⁵ areeach independently a C₆-C₁₂ aryl group and both L¹ and L² are a singlebond.
 4. The organic electric element of claim 1, Ar¹ to Ar⁴ are eachphenyl, Ar⁵ is biphenyl, and L¹ and L² are each independently a singlebond or phenylene.
 5. The organic electric element of claim 1, whereincompound represented by Formula 1 is any one of the compounds below:


6. The organic electric element of claim 1, wherein compound is a singlecompound or a mixture of two or more different kinds.
 7. An organicelectric element, comprising: a first electrode, a second electrode, andan organic material layer formed between the first electrode and thesecond electrode, and comprising at least a hole transport layer, anemission-auxiliary layer and a light emitting layer, wherein theemission-auxiliary layer comprises compound represented by Formula 1below, and the light emitting layer comprises compound represented byFormula 7 below,

wherein, Ar¹ to Ar⁵ are each independently selected from the groupconsisting of a C₆-C₂₄ aryl group; a fluorenyl group; a C₂-C₂₅heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si and P; a fused ring formed by a C₃-C₂₄aliphatic ring and a C₆-C₂₄ aromatic ring; a C₁-C₂₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group and the combination thereof, L¹ and L² are eachindependently selected from the group consisting of a single bond, aC₆-C₂₄ arylene group, a fluorenylene group, a C₂-C₂₄ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si and P, a fused ring formed by a C₃-C₂₄ aliphatic ring and aC₆-C₂₄ aromatic ring and the combination thereof, i) Ar⁶ and Ar⁷ areeach independently selected from the group consisting of a C₆-C₆₀ arylgroup; a fluorenyl group; a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P; a fused ring formed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group,-L′-N(R^(a)) (R^(b)) and the combination thereof, and ii) Ar⁶ and Ar⁷may be linked together to form a ring, Ar⁸ is any one of Formulas 7-a,7-b and 7-c below,

in formulas 7-a, 7-b and 7-c, Ar⁹ to Ar¹¹

are each independently selected from the group consisting of a C₆-C₆₀aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P; a fused ring formed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group,-L′-N(R^(a)) (R^(b)) and the combination thereof, i) R¹ to R³ are eachindependently selected from the group consisting of hydrogen, deuterium,halogen, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si and P, a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, aC₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxy group, aC₆-C₃₀ aryloxy group, -L′-N(R^(a)) (R^(b)) and the combination thereof,and ii) adjacent groups of R¹s to R³s may be linked together to form aring, and the group not forming a ring is the same as defined in theabove i), q, r and s are each an integer of 0 to 4, and each of pluralR¹s, R^(e)s and R³s may be same or different each other when q, r and sare each an integer of 2 or more, L³ and L⁵ are each independentlyselected from the group consisting of a C₆-C₆₀ arylene group, afluorenylene group, a fused ring formed by a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclic group containing at leastone heteroatom selected from the group consisting of O, N, S, Si and P,and the combination thereof, L⁴ is selected from the group consisting ofa single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a fusedring formed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, and the combinationthereof, L′ in Ar⁶, Ar⁷, Ar⁹ to Ar¹¹ and R¹ to R³ is selected from thegroup consisting of a single bond, a C₆-C₆₀ arylene group, afluorenylene group, a fused ring formed by a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring, and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P, and R^(a) and R^(b) in Ar⁶, Ar⁷, Ar⁹ to Ar¹¹ and R¹ are eachindependently selected from the group consisting of a C₆-C₆₀ aryl group;a fluorenyl group; a fused ring formed by a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Siand P, when Ar¹ to Ar⁷, Ar⁹ to Ar¹¹ and R¹ to R³ are each independentlyan aryl group, a fluorenyl group, a heterocyclic group, a fused ring, analkyl group, an alkenyl group, an alkoxy group, or an aryloxy group,each of Ar¹ to Ar⁷, Ar⁹ to Ar¹¹, and R¹ to R³ may be substituted withone or more substituents selected from the group consisting ofdeuterium; halogen; a silane group; a siloxane group; a boron group; agermanium group; a cyano group; a nitro group; a C₁-C₂₀ alkylthio group;a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; aC₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl groupsubstituted with deuterium; a fluorenyl group; a C₂-C₂₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si and P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀arylalkyl group; and a C₈-C₂₀ arylalkenyl group, and when L¹ to L⁵ areeach independently an arylene group, a fluorenylene group, aheterocyclic group or a fused ring, each of L¹ to L⁵ may be substitutedwith one or more substituents selected from the group consisting ofdeuterium; halogen; a silane group; a siloxane group; a boron group; agermanium group; a cyano group; a nitro group; a C₁-C₂₀ alkylthio group;a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; aC₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl groupsubstituted with deuterium; a fluorenyl group; a C₂-C₂₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si and P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀arylalkyl group; and a C₈-C₂₀ arylalkenyl group.
 8. The organic electricelement of claim 1, wherein Formula 7 is any one of the compounds below:


9. The organic electric element as claimed in claim 1, wherein theorganic electric element further including at least a layer to improveluminous efficiency which is formed on at least one of the sides thefirst and second electrodes, which is opposite to the organic materiallayer.
 10. The organic electric element as claimed in claim 1, whereinthe organic material layer is formed by any one of the process of spincoating, nozzle printing, inkjet printing, slot coating, dip coating androll-to-roll.
 11. An electronic device, comprising: a display devicewhich comprises the organic electric element of claim 1, and a controlunit for driving the display device.
 12. The electronic device of claim11, wherein the organic electric element comprises at least one of anorganic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic orwhite illumination.